JPH0547535B2 - - Google Patents

Info

Publication number: JPH0547535B2
Authority: JP; Japan
Prior art keywords: monomers; polymers; acid; monomer; group
Prior art date: 1981-08-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP57136445A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5841846A (ja

Inventor

Watokinsu Hatsuton Toomasu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rohm and Haas Co

Original Assignee

Rohm and Haas Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-08-07

Filing date

1982-08-06

Publication date

1993-07-19

1982-08-06 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1983-03-11 Publication of JPS5841846A publication Critical patent/JPS5841846A/ja

1993-07-19 Publication of JPH0547535B2 publication Critical patent/JPH0547535B2/ja

Status Granted legal-status Critical Current

Links

239000000178 monomer Substances 0.000 abstract description 55
229920000642 polymer Polymers 0.000 abstract description 19
239000002253 acid Substances 0.000 abstract description 12
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract description 10
238000000034 method Methods 0.000 abstract description 9
150000001450 anions Chemical class 0.000 abstract description 5
238000010438 heat treatment Methods 0.000 abstract description 5
125000000217 alkyl group Chemical group 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 3
238000004132 cross linking Methods 0.000 abstract description 3
229920000126 latex Polymers 0.000 abstract description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 20
229920001577 copolymer Polymers 0.000 description 14
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 11
-1 dialkylamine hydrogen Chemical class 0.000 description 11
150000003512 tertiary amines Chemical class 0.000 description 11
125000001453 quaternary ammonium group Chemical group 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000004908 Emulsion polymer Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
150000003856 quaternary ammonium compounds Chemical class 0.000 description 5
230000009257 reactivity Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229910002651 NO3 Inorganic materials 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000007334 copolymerization reaction Methods 0.000 description 4
229920001519 homopolymer Polymers 0.000 description 4
229910017604 nitric acid Chemical class 0.000 description 4
239000008188 pellet Substances 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
230000008961 swelling Effects 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
125000006353 oxyethylene group Chemical group 0.000 description 2
239000003505 polymerization initiator Substances 0.000 description 2
238000005956 quaternization reaction Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 2
235000018341 sodium sesquicarbonate Nutrition 0.000 description 2
WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 2
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
MLFIYYDKLNZLAO-UHFFFAOYSA-N 2-aminoethane-1,1-diol Chemical compound NCC(O)O MLFIYYDKLNZLAO-UHFFFAOYSA-N 0.000 description 1
KRGXWTOLFOPIKV-UHFFFAOYSA-N 3-(methylamino)propan-1-ol Chemical compound CNCCCO KRGXWTOLFOPIKV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
238000012644 addition polymerization Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000002009 alkene group Chemical group 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
PVEOYINWKBTPIZ-UHFFFAOYSA-M but-3-enoate Chemical compound [O-]C(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-M 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
LVYIGGHXRNEANI-UHFFFAOYSA-N butyl prop-2-enoate ethyl prop-2-enoate methyl 2-methylprop-2-enoate methyl prop-2-enoate Chemical compound C(C(=C)C)(=O)OC.C(CCC)OC(C=C)=O.C(C=C)(=O)OCC.C(C=C)(=O)OC LVYIGGHXRNEANI-UHFFFAOYSA-N 0.000 description 1
YWDYRRUFQXZJBG-UHFFFAOYSA-N butyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCCCOC(=O)C=C YWDYRRUFQXZJBG-UHFFFAOYSA-N 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical group 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000003999 initiator Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000004816 latex Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
AQJDUVPVFKXJCE-UHFFFAOYSA-N n-(2-cyclohexylethyl)-n-ethyldodecan-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCN(CC)CCC1CCCCC1 AQJDUVPVFKXJCE-UHFFFAOYSA-N 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
INHNQBQIGOOEGY-UHFFFAOYSA-N octadecan-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCCCCCCN INHNQBQIGOOEGY-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/14—Esters of polycarboxylic acids
- C08F18/16—Esters of polycarboxylic acids with alcohols containing three or more carbon atoms
- C08F18/18—Diallyl phthalate
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Paper (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polyesters Or Polycarbonates (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

JP57136445A 1981-08-07 1982-08-06 ハロヒドロキシプロピル第４アンモニウムモノマ− Granted JPS5841846A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US29114381A	1981-08-07	1981-08-07
US291143		1981-08-07

Publications (2)

Publication Number	Publication Date
JPS5841846A JPS5841846A (ja)	1983-03-11
JPH0547535B2 true JPH0547535B2 (da)	1993-07-19

Family

ID=23119039

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57136445A Granted JPS5841846A (ja)	1981-08-07	1982-08-06	ハロヒドロキシプロピル第４アンモニウムモノマ−

Country Status (15)

Country	Link
EP (1)	EP0072160B1 (da)
JP (1)	JPS5841846A (da)
AT (1)	ATE19091T1 (da)
AU (1)	AU565300B2 (da)
BR (1)	BR8204436A (da)
CA (1)	CA1184925A (da)
DE (1)	DE3270407D1 (da)
DK (1)	DK166350C (da)
ES (1)	ES514830A0 (da)
FI (1)	FI84056C (da)
IE (1)	IE53154B1 (da)
MX (1)	MX162324A (da)
NZ (1)	NZ201478A (da)
PH (1)	PH21704A (da)
ZA (1)	ZA825705B (da)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3678098A (en) *	1969-04-04	1972-07-18	Rohm & Haas	Unsaturated quaternary monomers and polymers
US3694393A (en) *	1969-04-04	1972-09-26	Rohm & Haas	Method of producing paper,and paper obtained

1982
- 1982-07-23 CA CA000407998A patent/CA1184925A/en not_active Expired
- 1982-07-26 PH PH27630A patent/PH21704A/en unknown
- 1982-07-29 BR BR8204436A patent/BR8204436A/pt not_active IP Right Cessation
- 1982-07-30 DE DE8282304032T patent/DE3270407D1/de not_active Expired
- 1982-07-30 EP EP82304032A patent/EP0072160B1/en not_active Expired
- 1982-07-30 AT AT82304032T patent/ATE19091T1/de active
- 1982-08-03 NZ NZ201478A patent/NZ201478A/en unknown
- 1982-08-05 MX MX193907A patent/MX162324A/es unknown
- 1982-08-05 IE IE1884/82A patent/IE53154B1/en not_active IP Right Cessation
- 1982-08-06 JP JP57136445A patent/JPS5841846A/ja active Granted
- 1982-08-06 FI FI822745A patent/FI84056C/fi not_active IP Right Cessation
- 1982-08-06 ES ES514830A patent/ES514830A0/es active Granted
- 1982-08-06 AU AU86938/82A patent/AU565300B2/en not_active Expired
- 1982-08-06 DK DK353982A patent/DK166350C/da not_active IP Right Cessation
- 1982-08-06 ZA ZA825705A patent/ZA825705B/xx unknown

Also Published As

Publication number	Publication date
MX162324A (es)	1991-04-25
NZ201478A (en)	1985-12-13
ZA825705B (en)	1983-09-28
FI822745A0 (fi)	1982-08-06
ES8308604A1 (es)	1983-09-16
DE3270407D1 (en)	1986-05-15
EP0072160B1 (en)	1986-04-09
PH21704A (en)	1988-01-27
CA1184925A (en)	1985-04-02
BR8204436A (pt)	1983-07-19
IE53154B1 (en)	1988-07-20
ES514830A0 (es)	1983-09-16
DK353982A (da)	1983-02-08
FI84056B (fi)	1991-06-28
DK166350C (da)	1993-09-06
FI84056C (fi)	1991-10-10
JPS5841846A (ja)	1983-03-11
DK166350B (da)	1993-04-13
IE821884L (en)	1983-02-07
EP0072160A1 (en)	1983-02-16
FI822745L (fi)	1983-02-08
AU565300B2 (en)	1987-09-10
ATE19091T1 (de)	1986-04-15
AU8693882A (en)	1983-02-10

Publication	Publication Date	Title
US3541059A (en)	1970-11-17	Novel reaction products of glycidyl esters and alkali metal sulfite or bisulfite,and polymers thereof
US3959205A (en)	1976-05-25	Preparation of aqueous emulsion
US5567527A (en)	1996-10-22	Copolymers containing 1,3-dioxolane-2-one-4-yl groups and coatings made therefrom
US6448330B1 (en)	2002-09-10	Aqueous emulsion and process for producing the same
US4642323A (en)	1987-02-10	Process for preparing latex polymers from gaseous monomers
JP3296580B2 (ja)	2002-07-02	超高分子量重合体エマルジョンの製造法
US4455411A (en)	1984-06-19	Process for preparing acrylamide polymers
JPH0547535B2 (da)	1993-07-19
JP2694388B2 (ja)	1997-12-24	グラフト基体とグラフトされた重合体相との間の相結合が向上したグラフトおよびコア・シェル共重合体
JPH0328442B2 (da)	1991-04-19
JPS6228803B2 (da)	1987-06-23
US5986031A (en)	1999-11-16	Process for making allylic copolymer resins
EP0072159A1 (en)	1983-02-16	Aromatic quaternary ammonium compounds, polymers thereof, polymerisable compositions containing them and methods of making the monomers and polymers
JPH0798849B2 (ja)	1995-10-25	硬化性水性樹脂分散液
EP0519097B1 (en)	1994-03-16	Process for the preparation of copolymers with units derived from glycidyl esters or glycidylethers
JP2734046B2 (ja)	1998-03-30	乳化重合体の製造方法
JPS5991102A (ja)	1984-05-25	カチオン性ラテツクスの製法
JP2725077B2 (ja)	1998-03-09	活性エステル型重合性界面活性剤
JPS617368A (ja)	1986-01-14	粘着剤組成物
JPS6239609A (ja)	1987-02-20	塩化ビニル系樹脂の製造方法
US20030191265A1 (en)	2003-10-09	Preparation of allylic copolymers of broad molecular weight distributions
JPH06192343A (ja)	1994-07-12	共重合体水溶液の製造方法
JPH0625217B2 (ja)	1994-04-06	変性アミン化合物の製造方法
JPS604503A (ja)	1985-01-11	カチオン性共重合体の製造方法
JPS6019929B2 (ja)	1985-05-18	共重合体の製造方法